September is a time of transition. This month finds summer officially giving way to fall. Moreover, this September 19—which boasts Bay View Bash, Global Union, and Country In The City—spells the conclusion of Milwaukee’s brief-but-busy festival season. Though the seasonal shift essentially puts a nine-month moratorium on outdoor events in town, local clubs and theaters are escalating the volume and the caliber of talent they book in effort to keep the entertainment coming as the temperatures outside dip. That said, Milwaukee isn’t exactly ending this summer with a whimper or lurching into autumn. Between the Chill On The Hill finale, a cluster of great comedians, respected bands in intimate settings, Mondo Lucha, and some unique movie screenings, this month of transition isn’t necessarily a bad thing. Of the abundance of awesome shit to do in Milwaukee this September, these 15 events stand out.

Tuesday, September 1
The Living Statues + Stephanie Erin Brill, and Dead Horses at Chill On The Hill (Humboldt Park)
Yet another Chill On The Hill concludes with one of the strongest shows of the season. Before The Living Statues brings its RedBull.com-approved pop-rock to the amphitheater, songstress Stephanie Erin Brill, and beer-inspiring folk trio Dead Horses—now with 66.6 percent Milwaukee residents!—will send the Bay View summer series out in grand fashion.

Wednesday, September 9
Jen Kirkman at Turner Hall
One of the funniest women/people/breathing organisms in contemporary comedy makes her Milwaukee headlining debut following her many memorable appearances on @midnight and Drunk History, as well as her uproariously funny new Netflix special I’m Gonna Die Alone (And I Feel Fine).

Mike Krol + Sat. Nite Duets, and Sin Bad at Cactus Club
Mike Krol’s hissy, distorted batch of shorthand garage rock has found him catching on with audiences across the country, as well as landing a spot on Merge Records. The Milwaukee ex-pat and brother of Hugh Bob & The Hustle drummer Justin Krol will come to Cactus Club for a homecoming show of sorts and will be joined by beloved locals Sat. Nite Duets and Sin Bad for an altogether outstanding hump day outing.

Friday, September 11
Tommy Stinson + The Obsoletes, and Beach Slang at Club Garibaldi
Those who missed The Replacements’ sold-out May 2 show at The Rave are in luck. Well, they’re sort of in luck, at least. Tommy Stinson, the bassist of the seminal Minneapolis rock band—and a little group called Guns N’ Roses—will return to Milwaukee with his own band to play what’s sure to be an unforgettable show at Bay View’s Club Garibaldi. Though he’s now based in New York, Stinson’s local ties run deep, as he’s represented by Ben Perlstein (formerly of the Benjamins) and recorded Midnight Reruns’ forthcoming and awesome full-length Force Of Nurture. Moreover, Jon Phillip (Good Land Records, Benjamins, Trapper Schoepp & The Shades) and Tim Schweiger (The Midwest Beat) used to serve as Stinson’s touring drummer and guitarist, respectively. Speaking of Phillip and Schweiger, their since-defunct band The Obsoletes (with Mystery Room Mastering owner Justin Perkins) will reunite to play this show as well, just months removed from their well-attended pair of early July shows. Philadelphia-based Beach Slang will also bring their Polyvinyl Records-caliber sound to the show’s opening slot.

Penn & Teller at Riverside Theater
Forget for a moment Penn & Teller, outspoken Libertarians and skeptics. Forget for a moment Penn & Teller, reality show staples. Forget for a moment Penn & Teller, creators of the brilliant/insufferable Bullshit! Instead, focus on Penn & Teller, entertainers and magicians. For nearly 40 years, the self-described “Bad Boys of Magic” have continually transformed their sometimes disreputable and corny profession into high art—all the while keeping things funny and delightfully morbid. Their long-running Las Vegas live show is a mind-bending Russian nesting doll of lies and deception, and a perfect example of why the duo are still vital to this day: they’re really fucking good at what they do. Milwaukee will get a chance to witness that magic firsthand when Penn (the taller, louder one) and Teller (the mostly silent one) bring their act to the Riverside Theater for the first time in 25 years.

Mondo Lucha at Turner Hall
In a night that also sees Tommy Stinson at Club Garibaldi and Penn & Teller at Riverside Theater, it’s hard to pick just one event. Buy hey, Milwaukee’s homegrown lucha libra wrestling blowout happens only once a year, and Whips are playing. Be there or be, you know, at one of those other shows we just mentioned.

Saturday, September 12
Rufus Wainwright with Milwaukee Symphony Orchestra at Marcus Center for the Performing Arts
Troubadour Rufus Wainwright is worth attendance and the price of admission alone. Add in accompaniment by the Milwaukee Symphony Orchestra, and this already enticing show becomes a rare requirement for any Rufus fan.

Monday, September 14
Desaparecidos + Joyce Manor at Turner Hall
Probably best known as “Conor Oberst’s old band,” Desaparecidos disbanded for a decade so the singer could focus on Bright Eyes. However, since it’s seemingly impossible for any band to remain dead these days, the Nebraska emo quintet reunited in 2012 with its full original lineup. Months removed from putting out Payola, the band’s first full-length since 2002, Obsert and company will drop by Turner Hall to play in support of its critically appreciated return record. California punk outfit Joyce Manor bolsters the lineup even more.

Friday, September 18
Hackers at Bike-In Movie Series + Caste Of Killers Showcase at Tire Swing Park
The Bike-In Movie Series is near perfection. A select few evenings each summer, people can bring their bikes (or arrive by any means of conveyance they decide) to a “park” beneath an East Side bridge to enjoy a free movie. The series is known to show massive blockbusters like Jurassic Park and lesser-known flicks like, say, Hackers. Prior to the under-appreciated 1995 thriller that introduced the world to Angelina Jolie, this near-perfect affair is improved even more with a pre-movie comedy show featuring Caste Of Killers comedy collective members Jason Hillman, Ryan Mason, and Addie Blanchardt

Saturday, September 19
Hannibal Buress at Riverside Theater
Since Hannibal Buress’ hilarious Turner Hall outing last year, his career trajectory has only gone up, as Broad City turned in a strong second season. He roasted Justin Bieber, and garnered some small parts in major studio comedies. Hannibal Buress: Live From Chicago (his latest special, which included material he performed at that Turner show) premiered on Comedy Central, and the network is currently running his new series, Why? Oh yeah, and he’s credited by many as the first person to publicly out Bill Cosby for his string of alleged sexual assaults. Somewhere during all that acting work and his ongoing climb to comic consciousness, Buress found time to write another hour of stand-up. He’s come a long way since doing sets at Milwaukee Comedy Cafe, which he considered to have “one of the worst comedy condos in the country” at the time.

Global Union at Humboldt Park
Bidding adieu to summer can be tough, especially considering the season lasts all of three months. Happily, Alverno Presents’ annual Global Union fest makes the end of the season go down a lot easier. For the past decade, the world-music fest has set up shop in Bay View’s Humboldt Park and thrown Milwaukee a diverse and dance-happy (and free!) goodbye party to summer.

Monday, September 21
Beach House + Jessica Pratt at Pabst Theater
Baltimore-based duo Beach House first came to widespread consciousness in indie rock circles with 2010’s Teenage Dream, and standout single “Zebra.” After that, the dream pop project’s popularity ebbed with 2012’s Bloom, but the tide is high again with the band’s brand new Depression Cherry, 45 minutes of delicate and downtrodden beauty that came out last week.

Tuesday, September 22
Wet Hot American Summer at The Avalon presented by Milwaukee Record
Fresh off the release of the Wet Hot American Summer: First Day Of Camp Netflix series, and with the final hours of summer ticking away, you can join us in watching an incomparably funny film that so many fell in love with long after its bewilderingly brief theatrical run. Even if you’ve seen Gene hump a refrigerator or watched McKinley and Ben make out dozens of times before, we’re willing to bet it wasn’t on the big screen. Though you might know Alan Shemper’s comedy routine by heart and can time the sound of breaking clay pots down to the nanosecond, both surely are even sweeter in surround sound. Have you ever witnessed Andy laboriously picking up his dishes while you were sitting in the company of 199 others in a place with a full-service bar? We’re going to guess you haven’t. Tickets for this special Milwaukee Record screening of an unforgettable cinematic summer standard are just $5 (plus $1 convenience fee), and they’re going fast.

Friday, September 25
Neil Hamburger at Club Garibaldi
For more than 20 years, comedian Gregg Turkington has gone on stage sporting a greased combover, an outdated suit, and Coke bottle glasses to adopt the persona of schlubby stand-up comic Neil Hamburger. With material that’s equal parts disgusting and entertaining, the long-running character has forged a unique comic voice that’s like if a Catskills comic had a recurring role in Troma films.

Friday, September 25 and Saturday, September 26
Garth Brooks + Trisha Yearwood at BMO Harris Bradley Center
Though we’d much prefer a Chris Gaines show, country legend Garth Brooks’ first Milwaukee shows in 19 years will do.